A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Osprey condo rentals

A covered patio with a sofa, a table, and potted plants.

1. Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (12 reviews)
"Great place- relaxed vibe"
United States
zachary p.
The price is AED 602
AED 1,835 total
includes taxes & fees
4 Nov - 5 Nov
Turtle Nest
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
The price is AED 565
AED 701 total
includes taxes & fees
4 Nov - 5 Nov
Captiva Beach Resort
A spacious room with a white ceiling fan, a beige sofa, a dining table with chairs, and large windows with blinds.

3. Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
Siesta Key
9.2 out of 10, Wonderful, (43 reviews)
"Excellent host, great location. I will come back again."
United States
Lu V.
The price is AED 768
AED 1,569 total
includes taxes & fees
4 Nov - 5 Nov
Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
A house with a gravel driveway, two blue chairs facing the front, and a porch with a green chair and a red umbrella.

4. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is AED 353
AED 889 total
includes taxes & fees
4 Nov - 5 Nov
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A wooden deck with a railing overlooking a calm river, surrounded by trees.

5. Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
Siesta Key
9.0 out of 10, Wonderful, (42 reviews)
"Siesta Heron is a gem! We loved having morning coffee on the deck by the water, the heated pool and the easy access to the trolley. Great location. The unit was clean and the hosts were extremely responsive and helpful!"
United States
Carrie B.
The price is AED 663
AED 1,181 total
includes taxes & fees
4 Nov - 5 Nov
Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
A pool area with palm trees, a small pool, and a wooden fence.

6. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveler
The price is AED 531
AED 1,130 total
includes taxes & fees
4 Nov - 5 Nov
Romantic Getaway Beach Club Siesta 202B by RVA
A rooftop lounge with a fire feature, seating, and a view of the cityscape.

7. Heated Pool Apartment Near Siesta Key 1BR

Heated Pool Apartment Near Siesta Key 1BR
Sarasota
9.2 out of 10, Wonderful, (47 reviews)
"The condo is small but it was clean and we had a great time. Short drive to Siesta Key public beach and close to shopping. Doris was a great host and answered any questions we had."
United States
Melissa M.
The price is AED 323
AED 996 total
includes taxes & fees
4 Nov - 5 Nov
Heated Pool Apartment Near Siesta Key 1BR
A balcony with a view of a pond, surrounded by trees and a grassy area.

8. The Perfect Shiny Condo

The Perfect Shiny Condo
Sarasota
9.4 out of 10, Exceptional, (20 reviews)
"The property could probably use some updating but the apartment was clean and had the needed essentials. Close and convenient driving distance to beaches. Good place to stay if you’re in Sarasota."
United States
Janneth A.
The price is AED 327
AED 881 total
includes taxes & fees
4 Nov - 5 Nov
The Perfect Shiny Condo
A pool area with palm trees, a small pool, and a wooden fence.

9. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
The price is AED 621
AED 1,511 total
includes taxes & fees
6 Nov - 7 Nov
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A covered outdoor area with a pool, lounge chairs, and a table with chairs.

10. Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach

Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach
Siesta Key
9.0 out of 10, Wonderful, (79 reviews)
"Nice place, great location,pool,and was nice having 2 grills on the property. "
United States
Nicholas H.
The price is AED 660
AED 1,199 total
includes taxes & fees
4 Nov - 5 Nov
Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance to Beach
A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

11. Updated unit with easy beach access on Siesta Key

Updated unit with easy beach access on Siesta Key
Siesta Key
9.2 out of 10, Wonderful, (89 reviews)
"Good location, everything was clean. Enjoyed beach access. Will stay again."
United States
Pat G.
The price is AED 709
AED 1,585 total
includes taxes & fees
4 Nov - 5 Nov
Updated unit with easy beach access on Siesta Key
A pool area with palm trees, a small pool, and a wooden fence.

12. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"Great beach! "
United States
Annie B.
The price is AED 624
AED 1,518 total
includes taxes & fees
4 Nov - 5 Nov
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
An aerial view of a coastal property with a large house, a beach, and a parking area.

13. Jetties Pointe Cottage #2 - 408 “Casey Key”

Jetties Pointe Cottage #2 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (15 reviews)
"Cute little beach cottage! It was perfect for my little family of 4. The location was great and the swings overlooking the beach were wonderful. "
United States
Kirstie C.
The price is AED 568
AED 1,408 total
includes taxes & fees
4 Nov - 5 Nov
Jetties Pointe Cottage #2 - 408 “Casey Key”
A covered outdoor patio with a stone floor, white lattice railings, and a table with chairs.

14. Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
South Village
10.0 out of 10, Exceptional, (22 reviews)
"The stay was nice!"
United States
John S.
The price is AED 891
AED 1,699 total
includes taxes & fees
8 Nov - 9 Nov
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
Private kitchen

15. 5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..

5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
Sarasota
9.4 out of 10, Exceptional, (28 reviews)
"Excellent location and really nice atmosphere"
United States
Eduardo V.
The price is AED 404
AED 1,465 total
includes taxes & fees
4 Nov - 5 Nov
5 minutes drive to nr Siesta Key 2BR/2BA condo Sienna Park. heated pool..
A modern kitchen with white cabinets, a central island with bar stools, and a built-in microwave.

16. Have fun at our Sunny Beachside Retreat remodeled head to toe!

Have fun at our Sunny Beachside Retreat remodeled head to toe!
South Village
9.8 out of 10, Exceptional, (16 reviews)
"Place was clean and nice.. deff good location close to beach and pool will be back soon"
United States
Oscar G.
The price is AED 698
AED 1,375 total
includes taxes & fees
4 Nov - 5 Nov
Have fun at our Sunny Beachside Retreat remodeled head to toe!
A deck with Adirondack chairs and a wooden post.

17. Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (13 reviews)
"Great location, spacious parking, clean."
United States
Norma C.
The price is AED 474
AED 1,114 total
includes taxes & fees
15 Nov - 16 Nov
Canalfront Siesta key entire King suite
A two-story house with a balcony, a patio with chairs, and a small garden area.

18. 5 Minutes from Siesta Key!

5 Minutes from Siesta Key!
Sarasota
9.4 out of 10, Exceptional, (54 reviews)
"Wonderful place to stay, super clean and comfortable. Communication was great."
United States
Cameron W.
The price is AED 731
AED 1,337 total
includes taxes & fees
22 Nov - 23 Nov
5 Minutes from Siesta Key!
A pool area with palm trees, a small pool, and a wooden fence.

19. 2BR Beach & Trolley–Beach Club Siesta 204B by RVA

2BR Beach & Trolley–Beach Club Siesta 204B by RVA
South Village
8.6 out of 10, Excellent, (48 reviews)
"Excellent"
United States
Yamila
The price is AED 584
AED 1,466 total
includes taxes & fees
4 Nov - 5 Nov
2BR Beach & Trolley–Beach Club Siesta 204B by RVA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

8/10 Good
"Perfect location near the airport. Appreciated the shuttle service."
Rosemarie 1-night trip
Posted 9 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from AED 701 to AED 1,835 per night. These stays provide loads of space for your whole crew at a price that's friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Osprey?
Choose from multiple condos in Osprey with a total average guest review rating of 9.4. Venice Beach Villas comes highly recommended if you're traveling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai.
How many condos are there in Osprey?
Work out your vacation dates and then pick from 3554 condos in Osprey. For an official business trip, a couples' getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks.
Are there any 5-star condos in Osprey?
Although there are no 5-star condos in Osprey, there are 4-star accommodations that have what you're looking for. Located about 11 kilometers from the downtown area, Gulf Holiday By Beachside Management comes with concierge services and a swimming pool. Another upscale retreat is Excelsior Beach To Bay - Bayside. It's roughly 8 kilometers from the center of Osprey and has amenities like a swimming pool and a deck.
Why book your condo in Osprey with Expedia?
With Expedia, it's a cinch to find your ideal condo in Osprey. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you have a set budget, select how much you're willing to spend and then browse our amazing options. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap condos in Osprey?
With Expedia's user-friendly filter tool, comparing cheap condos in Osprey is a snap. To discover properties that'll make your wallet happy, refine your search by amenities, budget and star rating.